After one season in Houston, Scottie Pippen asked for a trade and was dealt to the Portland Trail Blazers prior to the start of the 1999-00 season. The future Hall of Famer played in all 82 games in his first year in Portland, averaging 12.5 points, 6.3 rebounds and 5 assists per game. The Blazers finished the season with a record of 59-23, good enough for second place in the Pacific Division. They knocked out the Timberwolves in round one, the Jazz in the second round and faced the Lakers and Pippen's former coach Phil Jackson in the Western Conference Finals. The Blazers took the eventual champions to a game seven, with the Lakers defeating Portland in a tight contest by a score of 89-84.

The Trailblazers were founded in Portland in 1970 and are the only NBA team based in the bi-national Pacific Northwest. The unique Portland Trailblazers Pinwheel logo represents 5 offensive players & 5 defensive players coming together in the game of basketball.